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Fluorine and proton nmr studies of the conformations of 4,4-difluorocyclohexanol and its benzoate

Stolow, Robert D. and Giants, Thomas W. and Roberts, John D. (1968) Fluorine and proton nmr studies of the conformations of 4,4-difluorocyclohexanol and its benzoate. Tetrahedron Letters, 9 (55). pp. 5777-5780. ISSN 0040-4039. doi:10.1016/S0040-4039(00)76348-9.

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Fluorine substitution into a polar flexible molecule may be expected to significantly alter the conformational equilibria for that molecule because of electrostatic (or other) interactions between polar substituents and the fluorine atoms. Therefore, the “fluorine-labeling technique” which has been used successfully in conformational studies of hydrocarbons (4.5). should not be extended to polar flexible molecules without taking account of the interactions introduced by the fluorine atoms and their effect on the conformational energies. We report here studies of conformational equilibria by fluorine and proton nmr directed toward evaluation of the transannular interactions introduced when a 4,4-difluoro group is substituted into cyclohexanol (and other related polar flexible molecules).

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Additional Information:© 1968 Pergamon Press. Received in USA 31 July 1968; received in UK for publication 15 September 1968. Supported by the National Science Foundation. This investigation was supported in part by a Public Health Service Fellowship GM-38, 185-01 from the National Institute of General Medical Sciences. Acknowledgment is made to the donors of The Petroleum Research Fund, administered by the American Chemical Society for partial support of this research. Contribution No. 3716.
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U.S. Public Health Service (USPHS)GM-38185-01
American Chemical Society Petroleum Research FundUNSPECIFIED
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Caltech Gates and Crellin Laboratories of Chemistry3716
Issue or Number:55
Record Number:CaltechAUTHORS:20151026-114004986
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Official Citation:Robert D. Stolow, Thomas W. Giants, John D. Roberts, Fluorine and proton nmr studies of the conformations of 4,4-difluorocyclohexanol and its benzoate, Tetrahedron Letters, Volume 9, Issue 55, 1968, Pages 5777-5780, ISSN 0040-4039, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:61520
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 21:55
Last Modified:10 Nov 2021 22:50

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